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49 Houses

(2) Excellent 

19

Dramatic Cottage Literally Over a Waterfall

Vermont / Montgomery

Montgomery cottage

3 2 nights min

  • sleeps 3
  • 2 nights min
  • Beach / lakeside relaxation
  • Ski
  • Ask about children

Price per night from

$207

Price per night from

$207

Great rentals within 20 miles that match your search

Distance approx 3.11 km from Montgomery Show on Map

20

Valhalla Haus

Vermont / Montgomery Center

Montgomery Center house

3 7 4 nights min

  • 3 bedrooms
  • sleeps 7
  • 4 nights min
  • Child Friendly
  • Ask about pets

Price per night from

$327

Responds fast!
avg. 49 minutes

Price per night from

$327

Distance approx 2.24 km from Montgomery Show on Map

13

Log Home in Winter Wonderland, Ski, Splash or just Get Away - Pet Friendly

Vermont / Montgomery Center

Montgomery Center house

2 6 2 nights min

  • 2 bedrooms
  • sleeps 6
  • 2 nights min
  • Ski
  • Child Friendly
  • Pet Friendly

Price per night from

$217

Price per night from

$217

Distance approx 19.86 km from Montgomery

10

A Vermont Country Inn - Suite

Vermont / Fairfax

Fairfax b and b

1 4 1 night min

  • 1 bedroom
  • sleeps 4
  • 1 night min
  • Swimming pool
  • Child Friendly
  • Air conditioning

Price per night from

$143

Price per night from

$143

Distance approx 6.64 km from Montgomery

18

Jay Peak 5 Bed Townhome Ski-on Ski-Off

Northeast Kingdom / Jay

Jay house

5 12 4 nights min

  • 5 bedrooms
  • sleeps 12
  • 4 nights min
  • Child Friendly

Price per night from

$1,198

Price per night from

$1,198

Distance approx 17.15 km from Montgomery

(5) Excellent 

12

Metcalf Pond Cottage, Near Smugglers Notch

Vermont / Jeffersonville

Jeffersonville cottage

3 8 3 nights min

  • 3 bedrooms
  • sleeps 8
  • 3 nights min
  • Beach / lakeside relaxation
  • Nearest beach 0 mi
  • Child Friendly

Price per night from

$189

Responds fast!
avg. 3 hours 12 minutes

Price per night from

$189

Distance approx 12.62 km from Montgomery

15

**Beautiful Cozy Cottage on Lake Eden**

Vermont / Eden Mills

Eden Mills cottage

2 2 nights min

  • sleeps 2
  • 2 nights min
  • Nearest beach 0.7 mi
  • Air conditioning
  • Private garden

Price per night from

$52

Price per night from

$52

Distance approx 6.64 km from Montgomery

14

Luxury Ski-on Ski-off 3-Bed Condo

Northeast Kingdom / Jay

Jay house

3 8 2 nights min

  • 3 bedrooms
  • sleeps 8
  • 2 nights min
  • Child Friendly
  • Air conditioning

Price per night from

$745

Price per night from

$745

Distance approx 9.89 km from Montgomery Show on Map

14

*NEW LISTING* WYNDHAM SMUGGLERS NOTCH

Vermont / Jeffersonville

Jeffersonville villa

2 8 min stay varies

  • 2 bedrooms
  • sleeps 8
  • min stay varies
  • Swimming pool
  • Child Friendly
  • Air conditioning

Price per night from

$398

Responds fast!
avg. 1 hour 16 minutes

Price per night from

$398

Distance approx 9.89 km from Montgomery Show on Map

19

Wyndham Vacation Resorts Smugglers' Notch Vermont

Vermont / Stowe

Stowe condo

1 5 2 nights min

  • 1 bedroom
  • sleeps 5
  • 2 nights min
  • Swimming pool
  • Child Friendly
  • Air conditioning

Price per night from

$225

Price per night from

$225

Distance approx 0.1 km from Montgomery Show on Map

(2) Excellent 

21

Rustic Vermont Farm Near Jay Peak

Vermont / Montgomery Center

Montgomery Center house

3 11 3 nights min

  • 3 bedrooms
  • sleeps 11
  • 3 nights min
  • Child Friendly
  • Pet Friendly
  • Private garden

Price per night from

$342

Responds fast!
avg. 3 hours 45 minutes

Price per night from

$342

Distance approx 19.3 km from Montgomery

5

Ski in/ski out condo on the East's #1 family resort

Vermont / Jeffersonville

Jeffersonville condo

2 8 1 night min

  • 2 bedrooms
  • sleeps 8
  • 1 night min
  • Ski
  • Child Friendly

Price per night from

$451

Price per night from

$451

Distance approx 17.23 km from Montgomery

6

Beautifully Renovated and Furnished Post and Beam

Vermont / Jeffersonville

Jeffersonville house

3 8 2 nights min

  • 3 bedrooms
  • sleeps 8
  • 2 nights min
  • Child Friendly
  • Pet Friendly

Price per night from

$274

Price per night from

$274

Distance approx 9.89 km from Montgomery Show on Map

13

Smugglers' Notch * 2 Bedroom, Sleeps 8

Vermont / Cambridge

Cambridge condo

2 8 2 nights min

  • 2 bedrooms
  • sleeps 8
  • 2 nights min
  • Swimming pool
  • Ski
  • Child Friendly

Price per night from

$400

Price per night from

$400

Distance approx 19.26 km from Montgomery

(5) Average 

41

Strawberry Acres Cottages~Blueberry & Strawberry

Northeast Kingdom / Newport Center

Newport Center cottage

2 5 1 night min

  • 2 bedrooms
  • sleeps 5
  • 1 night min
  • Beach / lakeside relaxation
  • Ski
  • Child Friendly

Price per night from

$207

Responds fast!
avg. 49 minutes

Price per night from

$207

Distance approx 8.63 km from Montgomery

(5) Very Good 

13

Cozy Carmel Cottage near Jay Peak VT

Northeast Kingdom / Jay

Jay cottage

1 5 2 nights min

  • 1 bedroom
  • sleeps 5
  • 2 nights min
  • Child Friendly
“Relaxing and comfy...very close to Jay Peak!” I would recommend the Carmel Cottage to anyone who likes a comfy winter getaway. The skiing at Jay Peak makes all the relaxing well worth it!
…see more

Price per night from

$169

Price per night from

$169

Distance approx 10.82 km from Montgomery

7

Clean, cute and cozy Jay Peak view

Northeast Kingdom / Jay

Jay house

2 6 6 nights min

  • 2 bedrooms
  • sleeps 6
  • 6 nights min
  • Beach / lakeside relaxation
  • Child Friendly
  • Ask about pets

Price per night from

$109

Price per night from

$109

Distance approx 10.37 km from Montgomery

(1) Excellent 

18

JAY PEAKS COZY CAPE 3bdroom house 13min. from jay

Northeast Kingdom / Jay

Jay house

3 7 1 night min

  • 3 bedrooms
  • sleeps 7
  • 1 night min
  • Child Friendly

Price per night from

$286

Responds fast!
avg. 1 hour 57 minutes

Price per night from

$286

Distance approx 19.35 km from Montgomery

4

2 bed 2 bath Condo walk to all activities

Vermont / Jeffersonville

Jeffersonville apartment

2 7 7 nights min

  • 2 bedrooms
  • sleeps 7
  • 7 nights min
  • Child Friendly

Price per night from

$327

Price per night from

$327

Distance approx 16.87 km from Montgomery

24

NEW! Rustic 3BR Hyde Park Woodland Home w/ Porch!

Vermont / Hyde Park

Hyde Park house

3 6 min stay varies

  • 3 bedrooms
  • sleeps 6
  • min stay varies
  • Ski
  • Child Friendly
  • Pet Friendly

Price per night from

$155

Responds fast!
avg. 21 minutes

Price per night from

$155

Distance approx 11.63 km from Montgomery

7

StromHaus at Journeys End

Northeast Kingdom / Jay Peak

Jay Peak house

1 8 2 nights min

  • 1 bedroom
  • sleeps 8
  • 2 nights min
  • Child Friendly
  • Ask about pets
  • Private garden

Price per night from

$337

Price per night from

$337

Distance approx 8.64 km from Montgomery

(6) Very Good 

12

Carmel Loft near Jay Peak, Vermont

Northeast Kingdom / Jay Peak

Jay Peak apartment

1 4 2 nights min

  • 1 bedroom
  • sleeps 4
  • 2 nights min
  • Child Friendly

Price per night from

$143

Price per night from

$143

Distance approx 3.38 km from Montgomery Show on Map

13

Deer Run

Northeast Kingdom / Jay

Jay house

6 15 2 nights min

  • 6 bedrooms
  • sleeps 15
  • 2 nights min
  • Child Friendly
  • Pet Friendly
  • Private garden

Price per night from

$286

Price per night from

$286

Distance approx 17.79 km from Montgomery

22

Gregoire Castle

Northeast Kingdom / Irasburg

Irasburg house

4 8 2 nights min

  • 4 bedrooms
  • sleeps 8
  • 2 nights min
  • Child Friendly
  • Pet Friendly
  • Private garden

Price per night from

$1,711

Price per night from

$1,711

Distance approx 16.91 km from Montgomery

24

NEW! Farmhouse - 7 Mi to Craftsbury Outdoor Center

Northeast Kingdom / Irasburg

Irasburg house

4 8 min stay varies

  • 4 bedrooms
  • sleeps 8
  • min stay varies
  • Ski
  • Child Friendly

Price per night from

$252

Responds fast!
avg. 9 minutes

Price per night from

$252

Distance approx 18.76 km from Montgomery

22

3 Bedroom Home

Vermont / Jeffersonville

Jeffersonville house

3 6 2 nights min

  • 3 bedrooms
  • sleeps 6
  • 2 nights min
  • Child Friendly

Price per night from

$171

Price per night from

$171

Distance approx 7.75 km from Montgomery

17

Relaxation Retreat

Northeast Kingdom / Lowell

Lowell apartment

2 6 2 nights min

  • 2 bedrooms
  • sleeps 6
  • 2 nights min
  • Child Friendly

Price per night from

$114

Price per night from

$114

Distance approx 4.14 km from Montgomery Show on Map

7

Jay Peak Cabin: JaMari Acres

Vermont / Richford

Richford house

3 12 2 nights min

  • 3 bedrooms
  • sleeps 12
  • 2 nights min
  • Nearest beach 3 mi
  • Child Friendly
  • Private garden

Price per night from

$257

Price per night from

$257

Distance approx 13.83 km from Montgomery

24

Hidden Hill Top Getaway

Vermont / Johnson

Johnson house

4 15 2 nights min

  • 4 bedrooms
  • sleeps 15
  • 2 nights min
  • Child Friendly
  • Private garden

Price per night from

$685

Responds fast!
avg. 1 hour 53 minutes

Price per night from

$685

Distance approx 6.53 km from Montgomery

11

Jay Peak V311 Luxury Townhouse

Northeast Kingdom / Jay

Jay townhouse

4 10 min stay varies

  • 4 bedrooms
  • sleeps 10
  • min stay varies
  • Ski
  • Child Friendly

Price per night from

$628

Price per night from

$628

Distance approx 8.75 km from Montgomery

(2) Very Good 

16

Jay Brook Lodge

Northeast Kingdom / Jay

Jay house

4 16 min stay varies

  • 4 bedrooms
  • sleeps 16
  • min stay varies
  • Beach / lakeside relaxation
  • Child Friendly
  • Pet Friendly

Price per night from

$457

Price per night from

$457

Distance approx 6.52 km from Montgomery

12

Jay Peak Resort Stoney Path #602

Northeast Kingdom / Jay

Jay condo

2 10 2 nights min

  • 2 bedrooms
  • sleeps 10
  • 2 nights min
  • Child Friendly

Price per night from

$384

Price per night from

$384

Distance approx 9.61 km from Montgomery

16

Jay Peak Pine Grove House

Northeast Kingdom / Jay

Jay house

4 10 min stay varies

  • 4 bedrooms
  • sleeps 10
  • min stay varies
  • Child Friendly
  • Pet Friendly
  • Private garden

Price per night from

$228

Price per night from

$228

Distance approx 6.45 km from Montgomery

17

Jay Peak V125 Luxury Trail side Townhouse

Northeast Kingdom / Jay

Jay townhouse

5 14 min stay varies

  • 5 bedrooms
  • sleeps 14
  • min stay varies
  • Child Friendly

Price per night from

$800

Price per night from

$800

Distance approx 11.26 km from Montgomery

28

Serenity Falls Lodge - Jay Peak Area - 10 mins From Ski Hill - Private Waterfall

Northeast Kingdom / North Troy

North Troy house

3 8 3 nights min

  • 3 bedrooms
  • sleeps 8
  • 3 nights min
  • Child Friendly
  • Pet Friendly

Price per night from

$218

Price per night from

$218

Distance approx 10.72 km from Montgomery

17

Victorian Manor

Northeast Kingdom / Troy

Troy house

6 18 min stay varies

  • 6 bedrooms
  • sleeps 18
  • min stay varies
  • Child Friendly
  • Private garden

Price per night from

$453

Price per night from

$453

Distance approx 9.2 km from Montgomery

(2) Excellent 

21

Frost House Luxury Home in the Woods

Northeast Kingdom / Jay

Jay house

4 12 2 nights min

  • 4 bedrooms
  • sleeps 12
  • 2 nights min
  • Ski
  • Child Friendly
  • Pet Friendly

Price per night from

$514

Price per night from

$514

Distance approx 6.56 km from Montgomery

(1) Excellent 

29

Stylish ski-in/out getaway w/easy access to trails, golf, & downhill runs

Northeast Kingdom / Jay

Jay house

2 6 min stay varies

  • 2 bedrooms
  • sleeps 6
  • min stay varies
  • Child Friendly
  • Car not necessary

Price per night from

$61

Price per night from

$61